Transition from planar to nonplanar hydrogen bond networks in the solvation of aromatic dimers: Propofol2-(H2O)2-4

  1. León, I. 1
  2. Millán, J. 2
  3. Cocinero, E.J. 1
  4. Lesarri, A. 3
  5. Fernández, J.A. 1
  1. 1 Universidad del País Vasco/Euskal Herriko Unibertsitatea
    info

    Universidad del País Vasco/Euskal Herriko Unibertsitatea

    Lejona, España

    ROR https://ror.org/000xsnr85

  2. 2 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  3. 3 Universidad de Valladolid
    info

    Universidad de Valladolid

    Valladolid, España

    ROR https://ror.org/01fvbaw18

Revista:
Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment & General Theory

ISSN: 1089-5639

Año de publicación: 2013

Volumen: 117

Número: 16

Páginas: 3396-3404

Tipo: Artículo

DOI: 10.1021/JP401386Y SCOPUS: 2-s2.0-84876881656 WoS: WOS:000318211400016 GOOGLE SCHOLAR

Otras publicaciones en: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment & General Theory

Objetivos de desarrollo sostenible

Resumen

Propofol (2,6-diisopropylphenol) is probably the most widely used intravenous general anesthetic. In this work, the interaction of propofol dimer with 2-4 water molecules was analyzed. The molecular aggregates were formed by using supersonic expansions, which maintain the molecules confined in a cold, collision-free environment. The clusters were then examined by using a number of mass-resolved laser-based spectroscopic techniques, including 2-color REMPI (resonance enhanced multiphoton ionization), UV/UV hole burning, and IR/UV double resonance. Two isomers were found for each stoichiometry, whose final structures were determined by comparison between the experimental data and those from density-functional-theory calculations (M06-2X/6-31+G(d)). The analysis of the observed structures allows the conclusion that the water molecules always form hydrogen bond networks, whose contribution to the cluster's total binding energy increases with the number of water molecules. In the cluster with four water molecules, the two propofol molecules lose most of their contact points. In addition, the steric hindrance produces a change from cyclic to noncyclic hydrogen bond networks earlier than in similar systems. © 2013 American Chemical Society.